Living radical polymerization promoter

Abstract

An organobismuth compound represented by the formula (1) and a method for preparing a living radical polymer using the organobismuth compound. In the formula (1), R 1 to R 3 each represent a C1-C8 alkyl group, an aryl group, a substituted aryl group, an aromatic heterocyclic group or a group represented by the formula (2) where at least one of R 1 to R 3 is a group represented by the formula (2), wherein R 4 and R 5 each represent a C3-C8 alkyl group, an aryl group or a substituted aryl group, and R 6 to R 8 each represent a hydrogen atom, a C1-C8 alkyl group, an aryl group or a substituted aryl group.

1. An organobismuth compound represented by the formula (1) 
       
         
           
           
               
               
           
         
       
       wherein R 1 to R 3  each represent a C1-C8 alkyl group, an aryl group, a substituted aryl group, an aromatic heterocyclic group or a group represented by the formula (2) where at least one of R 1 and R 2  is a group represented by the following formula (2) 
       
         
           
           
               
               
           
         
       
       wherein R 4  and R 5  each represent a C3-C8 alkyl group, an aryl group or a substituted aryl group, and R 6  to R 8  each represent a hydrogen atom, a C1-C8 alkyl group, an aryl group or a substituted aryl group, and R 3  is a group other than the at least one of R 1  and R 2 . 
     
     
       2. A method for preparing the organobismuth compound represented by the formula (1) according to  claim 1 , the method comprising reacting a compound represented by the formula (3) with a compound represented by the formula (4) 
       
         
           
           
               
               
           
         
       
       wherein X represents a halogen atom, a C1-C8 alkyl group, an aryl group, a substituted aryl group or an aromatic heterocyclic group where at least one of Xs is a halogen atom, 
       
         
           
           
               
               
           
         
       
       wherein Y represents a hydrogen atom or an alkali metal, R 4  and R 5  each represent a C3-C8 alkyl group, an aryl group or a substituted aryl group, and R 6  to R 8  each represent a hydrogen atom, a C1-C8 alkyl group, an aryl group or a substituted aryl group,
 to obtain the organobismuth compound according to  claim 1 . 
 
     
     
       3. A radical polymerization promoter being a compound represented by the formula (1) according to  claim 1 . 
     
     
       4. A method for preparing a living radical polymer, the method comprising polymerizing a vinyl monomer using a living radical polymerization initiator and a compound represented by the formula (1) according to  claim 1 . 
     
     
       5. The method for preparing a living radical polymer of  claim 4 , wherein the living radical polymerization initiator is an organobismuth compound represented by the formula (7) 
       
         
           
           
               
               
           
         
       
       wherein R 10  and R 11  each represent a C1-C8 alkyl group, an aryl group, a substituted aryl group or an aromatic heterocyclic group, R 12  and R 13  each represent a hydrogen atom or a C1-C8 alkyl group, and R 14  represents an aryl group, a substituted aryl group, an aromatic heterocyclic group, an acyl group, an amido group, an oxycarbonyl group or a cyano group. 
     
     
       6. The method for preparing a living radical polymer of  claim 4 , wherein the living radical polymerization initiator is an organotellurium compound represented by the formula (8) 
       
         
           
           
               
               
           
         
       
       wherein R 15  represents a C1-C8 alkyl group, an aryl group, a substituted aryl group or an aromatic heterocyclic group, R 12  and R 13  each represent a hydrogen atom or a C1-C8 alkyl group, and R 14  represents an aryl group, a substituted aryl group, an aromatic heterocyclic group, an acyl group, an amido group, an oxycarbonyl group or a cyano group. 
     
     
       7. A living radical polymer obtained by polymerizing a vinyl monomer using a living radical polymerization initiator and a compound represented by the formula (1) according to  claim 1 . 
     
     
       8. A mixture of a living radical polymerization initiator and a compound represented by the formula (1) according to  claim 1 . 
     
     
       9. The organobismuth compound according to  claim 1 , wherein R 1  represents a group represented by the formula (2), and R 2  and R 3  each represent a C1-C4 alkyl group or a phenyl group.